4-Morpholinebutanenitrile → 4-(Morpholin-4-yl)butan-1-amine

HRID 56168Notes

Reaction equation

HRID 56168 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][C:16]#[N:17])[CH2:9][CH2:8]1>C1COCC1.O>[O:7]1[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][CH2:15][CH2:16][NH2:17])[CH2:9][CH2:8]1

Participants

5

Reactant 2

HCID 2945744-MorpholinebutanenitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 2336114-(Morpholin-4-yl)butan-1-amine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To anhydrous THF (70 mL) was added LiAlH4 (5.37 g, 142 mmol) in one portion. The mixture was stirred at 0° C. for 20 min, and a solution of 4-morpholinobutanenitrile (7.26 g, 47 mmol) in anhydrous THF (40 mL) was added dropwise. Upon the end of addition the mixture was refluxed for 4 h, then cooled to 0° C., diluted with water (20 mL) and filtered. The filtrate was concentrated in vacuo to give the crude product for the next step without further purification.

Workup

  1. additionUpon the end of addition the mixture
  2. temperaturewas refluxed for 4 h
  3. temperaturecooled to 0° C.
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-2c9a79470dd24e1c8cfc412f9d1e7bf0
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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